Chris Guillebeau: The Dusty-Footed Traveling Entrepreneur

When Projet Inkblot reached our first reader in Brunei Darussalam, we were floored, but first we had to look on a map to see exactly where that was. So imagine our utter amazement when we were first introduced to the work of Chris Guillebeau, a traveling entrepreneur, New York Times' best selling author, and blogger, who as of a few weeks ago, completed his goal to visit every single country in the world that he had the ability to visit. That's 193 countries in total! Chris connects with audiences in far reaching countries daily (that most people can't even pronounce, let alone know how to locate on a map), and offers readers brilliantly simple advice about running a business, living authentically, travel hacking, and the art of non-conformity--which is exactly what his blog is called.It's easy to envy someone with so many enormous accomplishments under his belt, and not see it as being attainable for oneself, but the truly inspiring thing about Chris is how much he cares about helping others achieve similarly bold goals. He does it by being transparent about his process, vulnerable to his loyal readers, and being an optimistic, accessible, and encouraging leader. He also gives pragmatic and action-oriented advice that is easy for even the most fear-ridden person to follow. Reading his blog posts and highly personalized newsletters, it's impossible not to be invigorated by his infectious spirit.

We were lucky to catch Chris right before he took his trip to his last of 193 countries, Norway. We were hoping to uncover his big secret to success, but what we found instead was the story of just a regular Portland dude who stayed persistent, consistent, and focused throughout the years to yield the results that he is able to show for today. Below is a mix of our Q&A, some of our favorite resources from his blog, and opportunities where you can also become a cyber-mentee of Chris' (like us), and join his international community of nonconforming adventurers.

Did you have lots of people around you living unconventionally that you modeled yourself after, or who helped you identify the way that you wanted to live?

Not really, at least not the first part. I think you have to find people who see the world in a similar way as you. Fortunately, once you go looking for them, they’re not usually hard to find.

Was there a website, or websites that inspired you to create an online community for entrepreneurs and travelers?

No website, but I knew there were plenty of independent people out there who wanted something different. I hoped to contribute something positive that didn’t currently exist, at least not in the specific way that AONC became.

How did you know that online was the format that you wanted to reach the world and inspire people?

Well, online is the only scalable way. I used to live in West Africa and had a great experience working individually with people, but if you want to reach people all over the world, you need some kind of platform. That's what I love about blogging—anyone can connect with a wide and disparate audience regardless of geography.

I reached out to you personally and asked for your help in asking for help, and being vulnerable. You basically told me to fear not! Which was both a good and bad answer for me. Bad because I wanted you to tell me a magical answer that would kill my fear, but good because you were absolutely right. Did others give you tough love when you were just figuring out your direction?

I didn't mean it as tough love; I just meant you needn’t be afraid in asking for help. Most people are good and most people will provide whatever help you need, when you need it.

Are there ever periods where you don’t have sustained bursts of ideas and energy, which lead you to question your path?

Yes, and those are frustrating! There's no easy answer to this problem, but it does help to create a certain structure for your work. Knowing what you need to do but needing help getting started is a lot easier than not knowing what to do.

Deadlines help too: if I know I have to post every Monday and Thursday, I'll be sure to do so. If I know my book is due on a certain date and there are numerous people at the publisher who have scheduled time to work on it, I need to honor my commitment to them.

But as mentioned, I too get stuck sometimes.

Everyone has a team. What does yours look like?

I have no employees and my team is pretty small. I do work with a couple of great designers and a genius developer. For the World Domination Summit, our annual event in Portland, we do have a growing group of part-time staff and volunteers that meets bi-monthly throughout the year, and then more often as we get closer to the big weekend in July.

When you first started out, did you have a target demographic that later changed as your work evolved?

No, I’ve never had a demographic at least in the traditional sense. Instead I have more of a psychographic, or people that identify based on shared values and ideals. They are all ages and backgrounds and come from more than 100 countries.

It seems like more and more people are taking the plunge and choosing to live ‘unconventionally’ now. What is special about our time where people are mustering up the courage seemingly more than ever before?

People have always been somewhat dissatisfied with traditional paths, but what's changed is that now there are far more alternatives than ever before. At the same time, there are also a lot more role models. Most people won't change their behavior based on something that an author or celebrity says—but when they see their friends, colleagues, or neighbors doing something new, some of them will feel personally inspired to make a change for themselves.

The $100 Startup is like a less cheesy, entrepreneurial Chicken Soup For the Soul, in that it uses so many great examples that anyone can refer to and feel reassured that the dream is possible for them. Was that book a one-shot deal, or will there be more like that to help people get their work off the ground?

I’m glad you liked it. I love writing books and hope to write many more. :)

What is one place in the world (that you traveled to) that you identified the most with, not necessarily culturally, but where you learned the most about yourself?

I like the qualification you included. Of all the places where I learned about myself, I'd certainly put Sierra Leone and Liberia (both in West Africa) at the top of the list. They aren't easy countries to travel in, but I had a great experience as a volunteer on a hospital ship. I continue to think of those places almost every day, even as I'm pursuing very different projects and doing different kinds of work.

Do you plan on setting new travel goals for yourself after you reach 193 countries?

Yes, but they'll be different. I'm not interested in revisiting all 193 countries or going to the moon or anything like that. What I want to do is work much more closely with our community of unconventional people from around the world. I'll keep traveling, in other words, but in a more focused way than before.

What is the single most memorable thing that a fan/supporter has ever expressed to you?

In different ways, people often express that reading AONC or The $100 Startup helps them to see that they are not alone. The first time I heard that statement, I knew I'd be doing this kind of work for a long time.